3,4,6-tri-O-benzyl-α-D-lyxo-hexopyranosyl (1-methoxy-1-methyl)ethyl peroxide | 1258495-68-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-benzyl-α-D-lyxo-hexopyranosyl (1-methoxy-1-methyl)ethyl peroxide
• CAS: 1258495-68-9
• 化学式: C₃₁H₃₈O₇
• 分子量: 522.639
• InChiKey: LHOSKLBAXLFRDI-SKKKGAJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  38.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-α-D-lyxo-hexopyranosyl (1-methoxy-1-methyl)ethyl peroxide 在 硫酸 作用下， 以 丙酮 为溶剂， 生成 3,4,6-tri-O-benzyl-2-deoxy-α-D-lyxohexopyranosyl hydroperoxide
  参考文献：
  名称：

  Glycosyl hydroperoxides derived from 2-deoxysugars

  摘要：

  Oxidation of 3,4,6-tri-O-benzyl-2-deoxy-D-glucose and D-galactose or their t-butyl glycosides to the corresponding glycosyl hydroperoxides can be performed with hydrogen peroxide in the presence of an acid catalyst. Several reaction conditions and their influence on the effectiveness of the oxidation are discussed. Separation of the alpha - and beta-anomers of the glycosyl hydroperoxides was achieved through mixed peroxide formation by reaction of the hydroperoxide group with 2-methoxypropene and subsequent deprotection. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.09.005
• 作为产物：
  描述：

  2-甲氧基丙烯 、 2,4,6-tri-O-benzyl-D-lyxo-hexopyranosyl hydroperoxide 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以68.9%的产率得到3,4,6-tri-O-benzyl-α-D-lyxo-hexopyranosyl (1-methoxy-1-methyl)ethyl peroxide
  参考文献：
  名称：

  Glycosyl hydroperoxides derived from 2-deoxysugars

  摘要：

  Oxidation of 3,4,6-tri-O-benzyl-2-deoxy-D-glucose and D-galactose or their t-butyl glycosides to the corresponding glycosyl hydroperoxides can be performed with hydrogen peroxide in the presence of an acid catalyst. Several reaction conditions and their influence on the effectiveness of the oxidation are discussed. Separation of the alpha - and beta-anomers of the glycosyl hydroperoxides was achieved through mixed peroxide formation by reaction of the hydroperoxide group with 2-methoxypropene and subsequent deprotection. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.09.005